Ethyl 5-formylisoxazole-3-carboxylate → 5-Formyl-1,2-oxazole-3-carboxylic acid

HRID 566894Notes

Reaction equation

HRID 566894 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH:11]=[O:12])[O:8][N:7]=1)=[O:5])C>O1CCOCC1.Cl>[CH:11]([C:9]1[O:8][N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1)=[O:12]

Participants

4

Reactant 1

HCID 14439317Ethyl 5-formylisoxazole-3-carboxylate

Product 1

HCID 212639535-Formyl-1,2-oxazole-3-carboxylic acidYield 86.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl-5-formylisoxazole-3-carboxylate (25 mg) in 1,4-dioxan (3 ml) and 2M hydrochloric acid (1 ml) was stirred and heated at reflux for 5 h.; cooled and the solvents removed in vacuo. The residue was triturated in diethyl ether. The solvent was removed and the residue dried to leave the title compound (18 mg) as an orange/brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h.
  3. temperaturecooled
  4. customthe solvents removed in vacuo
  5. customThe residue was triturated in diethyl ether
  6. customThe solvent was removed
  7. customthe residue dried

Sources & evidence

ORD record
ord-486282f9b1ce4c6199ec3c1cb5c64741
Source dataset
uspto-grants-2001_01
Patent number
US06177425B1

Reaction notes

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